A facile synthesis of polysubstituted pyrroles

Authors
Dieter, RK Yu, HY
Citation
Rk. Dieter et Hy. Yu, A facile synthesis of polysubstituted pyrroles, ORG LETT, 2(15), 2000, pp. 2283-2286
Citations number
50
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
15
Year of publication
2000
Pages
2283 - 2286
Database
ISI
SICI code
1523-7060(20000727)2:15<2283:AFSOPP>2.0.ZU;2-Y
Abstract
[GRAPHICS] alpha-Aminoalkylcuprates prepared from CUX . SLiCl (X = Cl, CN) and 1 equiv of an alpha-lithiocarbamate undergo conjugate addition reactions to alpha, beta-alkynyl ketones in moderate to good yields, affording E:Z mixtures of alpha,beta-enones. Treatment of the conjugate adducts with PhOH/TMSCl in CH 2Cl2, effected carbamate deprotection and cyclization to afford a flexible two-step synthesis of substituted pyrroles.